Ethyl­dimethyl­ammonium oxalate

The title crystal structure, C₄H₁₂N⁺·C₂HO₄⁻, contains discrete ethyl­dimethyl­ammonium cations and oxalate monoanions. Linear chains of oxalate monoanions are formed by strong O—H...O hydrogen bonds. These chains are further connected by N—H...O and C—H...O hydrogen bonds through ethyl­dimethyl­ammonium cations, forming channels along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.082
• Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.41
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C6     -   C7     ...       1.55 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Ethyldimethylammonium oxalate

Crystal data

C4H12N^+·C2HO4^−	F(000) = 352
Mr = 163.17	Dx = 1.305 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4871 reflections
a = 5.5953 (7) Å	θ = 3.4–25.5°
b = 9.3979 (9) Å	µ = 0.11 mm^−1
c = 15.804 (2) Å	T = 100 K
β = 92.158 (9)°	Block, colourless
V = 830.45 (17) Å^3	0.42 × 0.40 × 0.38 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer	1185 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 25.5°, θmin = 3.4°
Detector resolution: 1024x1024 with blocks 2x2 pixels mm^-1	h = −6→4
ω scans	k = −11→11
4871 measured reflections	l = −19→19
1545 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: difference Fourier map
wR(F^2) = 0.082	All H-atom parameters refined
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0778P)^2 + 0.1154P] where P = (Fo^2 + 2Fc^2)/3
1545 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.32227 (19)	0.76284 (12)	0.64853 (7)	0.0169 (3)
H1	0.251 (3)	0.7901 (18)	0.5974 (10)	0.033 (4)*
C2	0.4476 (3)	0.62461 (15)	0.63370 (10)	0.0234 (3)
H2A	0.580 (3)	0.6475 (15)	0.5953 (9)	0.025 (4)*
H2B	0.514 (3)	0.5953 (16)	0.6899 (10)	0.028 (4)*
C3	0.2850 (3)	0.51297 (18)	0.59364 (11)	0.0354 (4)
H3A	0.211 (3)	0.5470 (19)	0.5393 (12)	0.049 (5)*
H3B	0.154 (3)	0.4823 (19)	0.6324 (12)	0.054 (5)*
H3C	0.389 (3)	0.427 (2)	0.5801 (10)	0.047 (5)*
C4	0.1365 (3)	0.7525 (2)	0.71296 (9)	0.0273 (4)
H4A	0.062 (3)	0.8492 (17)	0.7191 (9)	0.030 (4)*
H4B	0.216 (3)	0.7232 (16)	0.7679 (9)	0.027 (4)*
H4C	0.010 (3)	0.6819 (17)	0.6942 (10)	0.034 (4)*
C5	0.5010 (3)	0.87443 (15)	0.67299 (9)	0.0207 (3)
H5A	0.416 (2)	0.9655 (16)	0.6792 (9)	0.027 (4)*
H5B	0.618 (3)	0.8819 (15)	0.6289 (10)	0.025 (4)*
H5C	0.584 (2)	0.8470 (14)	0.7274 (9)	0.019 (4)*
C6	0.1929 (2)	0.83605 (13)	0.41414 (8)	0.0145 (3)
C7	−0.0529 (2)	0.83348 (13)	0.45655 (8)	0.0142 (3)
O8	0.37214 (15)	0.83389 (10)	0.46948 (5)	0.0187 (2)
H8	0.550 (4)	0.840 (2)	0.4389 (11)	0.069 (7)*
O9	−0.05736 (15)	0.81220 (11)	0.53368 (6)	0.0235 (3)
O10	−0.23153 (15)	0.85160 (10)	0.40610 (5)	0.0178 (2)
O11	0.20779 (16)	0.83820 (10)	0.33787 (6)	0.0236 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0159 (6)	0.0226 (6)	0.0122 (6)	0.0002 (5)	−0.0012 (4)	0.0027 (5)
C2	0.0279 (8)	0.0178 (8)	0.0240 (8)	0.0023 (6)	−0.0038 (7)	0.0003 (6)
C3	0.0441 (10)	0.0272 (9)	0.0344 (10)	−0.0076 (8)	−0.0055 (8)	−0.0020 (7)
C4	0.0197 (8)	0.0456 (10)	0.0165 (8)	−0.0027 (7)	0.0012 (6)	0.0024 (7)
C5	0.0221 (8)	0.0201 (8)	0.0198 (8)	−0.0015 (6)	−0.0017 (6)	0.0007 (6)
C6	0.0138 (7)	0.0152 (7)	0.0143 (7)	−0.0011 (5)	−0.0020 (5)	−0.0011 (5)
C7	0.0139 (7)	0.0149 (7)	0.0137 (7)	−0.0016 (5)	−0.0006 (5)	−0.0010 (5)
O8	0.0117 (5)	0.0314 (6)	0.0128 (5)	−0.0008 (4)	−0.0020 (4)	0.0027 (4)
O9	0.0145 (5)	0.0434 (7)	0.0127 (5)	0.0004 (4)	0.0005 (4)	0.0046 (4)
O10	0.0114 (5)	0.0276 (6)	0.0140 (5)	0.0004 (4)	−0.0024 (4)	0.0013 (4)
O11	0.0169 (5)	0.0413 (6)	0.0126 (5)	−0.0046 (4)	0.0006 (4)	−0.0030 (4)

Geometric parameters (Å, º)

N1—C4	1.485 (2)	C4—H4B	1.000 (15)
N1—C5	1.490 (2)	C4—H4C	1.007 (17)
N1—C2	1.499 (2)	C5—H5A	0.985 (15)
N1—H1	0.924 (16)	C5—H5B	0.977 (17)
C2—C3	1.512 (2)	C5—H5C	0.996 (14)
C2—H2A	1.000 (16)	C6—O11	1.212 (2)
C2—H2B	0.989 (15)	C6—O8	1.306 (1)
C3—H3A	0.993 (18)	C6—C7	1.552 (2)
C3—H3B	1.013 (19)	C7—O9	1.237 (2)
C3—H3C	1.027 (19)	C7—O10	1.266 (2)
C4—H4A	1.007 (16)	O8—H8	1.12 (2)
C4—N1—C5	110.38 (11)	N1—C4—H4B	108.2 (9)
C4—N1—C2	113.21 (12)	H4A—C4—H4B	109.8 (12)
C5—N1—C2	109.71 (11)	N1—C4—H4C	110.2 (9)
C4—N1—H1	109.3 (10)	H4A—C4—H4C	109.4 (13)
C5—N1—H1	107.1 (10)	H4B—C4—H4C	111.1 (13)
C2—N1—H1	107.0 (10)	N1—C5—H5A	108.5 (8)
N1—C2—C3	112.91 (13)	N1—C5—H5B	109.1 (9)
N1—C2—H2A	105.7 (8)	H5A—C5—H5B	110.2 (12)
C3—C2—H2A	110.1 (8)	N1—C5—H5C	109.2 (8)
N1—C2—H2B	105.3 (9)	H5A—C5—H5C	110.4 (11)
C3—C2—H2B	112.5 (9)	H5B—C5—H5C	109.4 (11)
H2A—C2—H2B	109.9 (11)	O11—C6—O8	125.9 (1)
C2—C3—H3A	111.4 (10)	O11—C6—C7	121.7 (1)
C2—C3—H3B	112.4 (10)	O8—C6—C7	112.4 (1)
H3A—C3—H3B	109.1 (14)	O9—C7—O10	126.7 (1)
C2—C3—H3C	107.3 (9)	O9—C7—C6	118.6 (1)
H3A—C3—H3C	107.3 (13)	O10—C7—C6	114.7 (1)
H3B—C3—H3C	109.3 (14)	C6—O8—H8	112.4 (9)
N1—C4—H4A	108.2 (9)
C4—N1—C2—C3	66.52 (16)	O8—C6—C7—O9	−8.8 (2)
C5—N1—C2—C3	−169.69 (13)	O11—C6—C7—O10	−8.4 (2)
O11—C6—C7—O9	170.4 (1)	O8—C6—C7—O10	172.4 (1)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O8	0.92 (2)	2.19 (2)	2.931 (1)	136 (1)
N1—H1···O9	0.92 (2)	1.98 (2)	2.781 (1)	144 (1)
O8—H8···O10^i	1.12 (2)	1.35 (2)	2.473 (1)	177 (2)
C4—H4B···O10^ii	1.00 (2)	2.30 (2)	3.264 (2)	161 (1)
C5—H5A···O10^iii	0.99 (2)	2.40 (2)	3.213 (2)	140 (1)
C5—H5B···O9^i	0.98 (2)	2.49 (2)	3.421 (2)	160 (1)
C5—H5C···O11^ii	1.00 (1)	2.54 (1)	3.449 (2)	151 (1)

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+3/2, z+1/2; (iii) −x, −y+2, −z+1.